Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 26, Pages 5061-5070Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100734
Keywords
Microwave chemistry; Spiro compounds; Rearrangement; Olefin metathesis; Michael addition
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Funding
- French Research Ministry
- Aix-Marseille Universite
- Centre National de la Recherche Scientifique (CNRS)
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A general synthetic route to alpha-spirolactones and -lactams from 2-diazo-1,3-dicarbonyl compounds, (homo)allylic alcohols or amines and acrylic dertivatives, involving a single consecutive reaction consisting of a Wolff rearrangement/alpha-oxo ketene trapping/cross metathesis/Michael addition sequence is described. During the consecutive reaction optimization, the organocatalytic activity of N,N-diaryl-1,3-imidazol(in)-2-ylidene N-heterocyclic carbenes (NHCs) in the Michael addition of 1,3-dicarbonyl compounds was discovered. A conceptually attractive version of the consecutive reaction was then developed, involving the Grubbs-Hoveyda ruthenium-based precatalyst containing the SIMes [1,3-bis (2,4, 6 -trimethylphenyl)imidazolin-2-ylidene] NHC ligand as the source of both the organometallic catalyst of the cross metathesis and the organic catalyst of the intramolecular Michael addition.
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